Head Of Harbor Real Estate

Welcome to Head of the Harbor, a picturesque village nestled in the heart of Suffolk County, New York. This charming community, known for its serene landscapes and rich history, offers an idyllic escape from the hustle and bustle of city life while still being conveniently located near the vibrant amenities of Long Island.

Head of the Harbor is renowned for its stunning waterfront views, with the picturesque shores of the Long Island Sound providing a serene backdrop for outdoor activities and leisurely strolls. The village is characterized by its lush greenery, sprawling estates, and a strong sense of community, making it a perfect place for families and individuals seeking tranquility and natural beauty.

One of the highlights of Head of the Harbor is its commitment to preserving its historical charm. With beautifully maintained homes that reflect a variety of architectural styles, residents enjoy a neighborhood that feels both timeless and inviting. The local parks and nature reserves offer ample opportunities for hiking, birdwatching, and enjoying the great outdoors.

Additionally, Head of the Harbor is conveniently located near some of Long Island's finest dining, shopping, and cultural attractions. Whether you're exploring the local art scene or indulging in gourmet cuisine, you'll find that this village is a hidden gem that perfectly balances rural charm with modern conveniences.

With its enchanting atmosphere, rich history, and close-knit community spirit, Head of the Harbor is not just a place to live—it's a lifestyle. Discover your dream home in this captivating village and experience the best that New York has to offer.

Newest Listings in Head Of Harbor

$3,790,000

5 Beds ⋅ 8 Baths ⋅ 1000931 MLS

Have you ever dreamed of building your own CUSTOM HOME in a small village on Long Island? Look No Further! Set within one of Long Island’s most prestigious and private villages, this extraordinary custom-built estate offers over 7,000 square feet of refined living space with an Elevator to service all Floors, First Floor Primary Suite, radiant floors, 2 Saunas, 2 steam showers, full basement with full bathroom and outside entrance, outside back porch with fireplace and full bathroom from outside only. Private setting on a breathtaking 2.35-acre wooded property, complemented by an additional one-acre private driveway. A seamless blend of timeless architecture and modern luxury, this residence has been thoughtfully designed with superior craftsmanship and uncompromising quality throughout. Home is completed to a point where we can schedule tours. A sweeping asphalt and stone driveway with cobblestone edging welcomes you to this impressive two-story traditional home. Inside, an elevator to service all floors of the home, soaring ceilings create an unparalleled sense of space — including a dramatic 20'6" two-story foyer and family room, 10-foot ceilings on the main level, and a full 10-foot walk-out basement offering endless possibilities. Main Level Elegance. The heart of the home is a spectacular chef’s kitchen featuring: * Custom cabinetry * Granite or Quartz countertops * Expansive center island with prep sink * Radiant-heated porcelain flooring Entertain effortlessly in the formal dining room with built-in cabinetry, elegant millwork, and premium stone surfaces. The two-story family room showcases a modern linear gas fireplace beneath a coffered ceiling, creating a striking focal point. An en-suite bedroom provides flexibility for guests or extended family. Additional highlights include a radiant-heated powder room and a covered rear porch with gas fireplace — perfect for year-round outdoor living. Upper-Level Retreat: The second floor features **four en-suite bedrooms**, each with custom closet systems and wide White Oak flooring. The primary suite is a sanctuary, boasting a spa-inspired bath with a large steam shower, radiant heated floors, and deluxe Kohler fixtures. Exceptional Construction & Infrastructure: Built for longevity and performance, this estate includes: * Engineered wood web floor joists *Oversize 3 Car Attached Garage * 400-amp electric service * Natural gas service for heating, hot water, dryer, future generator & pool * Public water via Suffolk County Water Authority * Seven oversized drywells for optimal drainage Throughout the home, meticulous detailing includes wide White Oak hardwood flooring, heavy base moldings, chair rail and crown moldings, and an extra-wide custom staircase with open railings. In-ground Pool is an option and can be customized. 3D Reality Tours are samples of the builders work, not the exact same model we are building. A rare opportunity to own a masterfully constructed estate in one of Long Island’s most exclusive enclaves — where privacy, luxury, and timeless design converge.

550 Moriches Road, Head Of Harbor

$1,199,999

993325 MLS

BUILD YOUR DREAM HOME!!!!!! A rare find....flat piece of land in the Incorporated village of Head of The Harbor. This property is surrounded by 4000-7000 sq foot homes. There is electric, water and gas at the property. Ideal location close to Stony Brook Hospital, and major roads.

Timothy Road, Head Of Harbor

$2,399,999

8 Beds ⋅ 8 Baths ⋅ 976021 MLS

New Price. Fresh Presentation. One Extraordinary Opportunity. *A Private Resort Where Luxury Meets Everyday Living* Motivated seller has thoughtfully repositioned this exceptional estate with a compelling new price, creating a rare opportunity to own one of Head of the Harbor's most distinctive luxury residences. Hidden at the end of a quiet cul de sac in the prestigious Incorporated Village of Head of the Harbor, 9 Watercrest Court is more than a home. It is a private retreat where holidays become traditions, generations gather, and every weekend feels like a vacation. Thoughtfully designed for exceptional entertaining and everyday living, every space encourages connection while offering the privacy and comfort of a true estate. Spanning approximately 10,000 square feet across all levels, the residence seamlessly blends timeless architecture with modern luxury. A dramatic two story foyer leads to expansive living spaces filled with natural light, soaring ceilings, radiant heated floors, custom millwork, and walls of windows. At the center of it all is a spectacular chef's kitchen featuring Wolf, Sub Zero, and Miele appliances, an oversized island, walk in pantry, coffee bar, and effortless flow into the surrounding gathering spaces. The primary suite offers a peaceful retreat with a spa inspired bath and oversized walk in closets, while the private guest residence, complete with its own kitchen, living room, bedroom, full bath, and separate entrance, provides exceptional flexibility for multigenerational living, extended family, long term guests, live in support, or a private executive suite. Designed for entertaining on a level rarely found in residential real estate, the lower level features a professionally designed private bowling alley, fitness area, recreation spaces, and multiple gathering areas that make birthdays, holidays, game nights, and family celebrations unforgettable. Outside, the resort style backyard offers an in ground pool, expansive patios, beautifully landscaped grounds, and multiple outdoor living spaces designed for everything from peaceful mornings with coffee to summer barbecues and evenings with family and friends. Ideally located in one of Long Island's most sought after North Shore communities, Head of the Harbor offers estate living just minutes from Stony Brook University, renowned hospitals, yacht clubs, golf courses, beaches, fine dining, and major transportation. This is more than a luxury home. It is where your family's next chapter begins. Notable Features • Approximately 10,000 square feet across all levels • Private guest residence with separate entrance • Professionally designed private bowling alley • Resort style in ground pool with expansive outdoor entertaining areas • Chef's kitchen with Wolf, Sub Zero, and Miele appliances • Radiant heated floors • Whole house generator • Fitness area and expansive recreation spaces • Located in the prestigious Incorporated Village of Head of the Harbor

9 Watercrest Court, Head Of Harbor

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.